用于水中苦味酸检测的咪唑衍生物的合成及其应用
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摘要
通过Debus-Radziszewski、Suzuki-Miyaura和Knoevenagel缩合反应,设计合成了一种新型的咪唑衍生物L,并使用傅里叶变换红外光谱和核磁共振氢谱对合成化合物进行了结构表征。不同极性溶剂中光物理性质和密度泛函理论计算结果表明该系列化合物具有典型的分子内电荷转移(Intramolecular charge transfer,ICT)效应;紫外-可见吸收和荧光发射光谱证实它表现出聚集诱导猝灭(Aggregation-caused quenching,ACQ)性质。进一步的光物理性质测试表明化合物L在THF/H_2O混合溶液中可实现对2,4,6-三硝基苯酚(苦味酸,picric acid,PA)的检测,检测限为3.7×10~(-6) mol/L。
A novel imidazole derivative L with electron-donating ability was designed and synthesized via the reactions of Debus-Radziszewski, Suzuki-Miyaura and Knoevenagel and characterized by FT-IR, ~1H NMR. The photophysical properties in different polar solvents and density functional theory calculation results demonstrated that L exhibited typical intramolecular charge transfer(ICT) effect. The UV-Vis spectra and fluorescence spectra showed that L exhibited aggregation-caused quenching(ACQ) properties. The test results show that L can achieve the detection for PA(picric acid) in THF/H_2O solution, and the limit of detection for PA is 3.7×10~(-6) mol/L.
A novel imidazole derivative L with electron-donating ability was designed and synthesized via the reactions of Debus-Radziszewski, Suzuki-Miyaura and Knoevenagel and characterized by FT-IR, ~1H NMR. The photophysical properties in different polar solvents and density functional theory calculation results demonstrated that L exhibited typical intramolecular charge transfer(ICT) effect. The UV-Vis spectra and fluorescence spectra showed that L exhibited aggregation-caused quenching(ACQ) properties. The test results show that L can achieve the detection for PA(picric acid) in THF/H_2O solution, and the limit of detection for PA is 3.7×10~(-6) mol/L.
引文
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[2] 余颖昊,杜斌,丁志军,等. 萘酰亚胺衍生物的合成及对苦味酸的检测 [J]. 发光学报, 2015,36(1):39-44. YU Y H,DU B,DING Z J,et al.. Synthesis of naphthalimide derivatives and its recognition for picric acid [J]. Chin. J. Lumin., 2015,36(1):39-44. (in Chinese)
[3] DING A X,YANG L M,ZHANG Y Y,et al.. Complex-formation-enhanced fluorescence quenching effect for efficient detection of picric acid [J]. Chem. Eur. J., 2014,20(38):12215-12222.
[4] SHANMUGARAJ K,JOHN S A. Inner filter effect based selective detection of picric acid in aqueous solution using green luminescent copper nanoclusters [J]. New J. Chem., 2018,42(9):7223-7229.
[5] PONNUVEL K,BANUPPRIYA G,PADMINI V. Highly efficient and selective detection of picric acid among other nitroaromatics by NIR fluorescent organic fluorophores [J]. Sens. Actuators B Chem., 2016,234:34-45.
[6] XU Y Q,LI B H,LI W W,et al.. “ICT-not-quenching” near infrared ratiometric fluorescent detection of picric acid in aqueous media [J]. Chem. Commun., 2013,49(42):4764-4766.
[7] ZHANG Y Y,PAN J T,ZHANG C Y,et al.. High quantum yield both in solution and solid state based on cyclohexyl modified triphenylamine derivatives for picric acid detection [J]. Dyes Pigm., 2015,123:257-266.
[8] 李康. 气相色谱法检测水中苦味酸试验 [J]. 现代农业科技, 2017,(10):177. LI K. Determination of picric acid in water by gas chromatography [J]. Mod. Agric. Sci. Technol., 2017(10):177.(in Chinese)
[9] 张宗祥,翟有朋,张颖. 高效液相色谱法测定水中苦味酸 [J]. 中国测试, 2017,43(9):59-63. ZHANG Z X,ZHAI Y P,ZHANG Y. Determination of picric acid in water by high performance liquid chromatography [J]. China Measur. Test Technol., 2017,43(9):59-63. (in Chinese)
[10] 赵红帅,常淼,刘保献,等. 高效液相色谱法快速测定水中苦味酸 [J]. 中国环境监测, 2013,29(4):135-137. ZHAO H S,CHANG M,LIU B X,et al.. Quickly determination of pricia acid in water by high performance liquid chromatography [J]. Environ. Monit. China, 2013,29(4):135-137. (in Chinese)
[11] 吴斌,苏宇亮,吴杰,等. 离子色谱法分析地表水中的苦味酸 [J]. 净水技术, 2018,37(3):50-52. WU B,SU Y L,WU J,et al.. Determination of picric acid in surface water by ion chromatography [J]. Water Purif. Technol., 2018,37(3):50-52. (in Chinese).
[12] 王书民,樊雪梅,白晓晶,等. KMnO4-乙二醛化学发光法测定苦味酸 [J]. 分析试验室, 2011,30(8):57-59. WANG S M,FAN X M,BAI X J,et al.. Potassium permanganate-glyoxal chemiluminescence system for determination of picric acid [J]. Chin. J. Anal. Lab., 2011,30(8):57-59. (in Chinese)
[13] ADIL L R,GOPIKRISHNA P,IYER P K. Receptor-free detection of picric acid:a new structural approach for designing aggregation-induced emission probes [J]. ACS Appl. Mater. Interfaces, 2018,10(32):27260-27268.
[14] WANG F Y,GUO Z Q,LI X,et al.. Development of a small molecule probe capable of discriminating cysteine,homocysteine,and glutathione with three distinct turn-on fluorescent outputs [J]. Chem. Eur. J., 2014,20(36):11471-11478.
[15] KUSHWAHA A,PATIL S K,DAS D. A pyrene-benzimidazole composed effective fluoride sensor:potential mimicking of aboolean logic gate [J]. New J. Chem., 2018,42(11):9200-9208.
[16] JIGYASA,RAJPUT J K. “ON-OFF” novel fluorescent chemosensors based on nanoaggregates of triaryl imidazoles for superselective detection of nitro-explosive trinitrophenol in multiple solvent systems [J]. Sens. Actuators B Chem., 2018,259:990-1005.
[17] ZHANG Y Y,HUANG J Y,KONG L,et al.. Two novel AIEE-active imidazole/α-cyanostilbene derivatives:photophysical properties,reversible fluorescence switching,and detection of explosives [J]. Cryst Eng. Comm., 2018,20(9):1237-1244.
[18] ZHANG X Q,CHI Z G,XU B J,et al.. Multifunctional organic fluorescent materials derived from 9,10-distyrylanthracene with alkoxyl endgroups of various lengths [J]. Chem. Commun., 2012,48(88):10895-10897.
[19] KUNDU A,LEE J,PARK B,et al.. Facile approach to synthesize highly fluorescent multicolor emissive carbon dots via surface functionalization for cellular imaging [J]. J. Colloid Interface Sci., 2018,513:505-514.
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